Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

Aoi Takeda; Toru Komatsu; Hiroshi Nomura; Masamitsu Naka; Norio Matsuki; Yuji Ikegaya; Takuya Terai; Tasuku Ueno; Kenjiro Hanaoka; Tetsuo Nagano; Yasuteru Urano

doi:10.1002/cbic.201600097

Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

Aoi Takeda, Toru Komatsu, Hiroshi Nomura, Masamitsu Naka, Norio Matsuki, Yuji Ikegaya, Takuya Terai, Tasuku Ueno, Kenjiro Hanaoka, Tetsuo Nagano, Yasuteru Urano

研究成果: Article › 査読

13 被引用数 (Scopus)

抄録

Investigation of the unexpected photo-instability of 2,6-sulfonamide-substituted derivatives of the boron dipyrromethene (BODIPY) fluorophore led to the discovery of a photoreaction accompanied by multiple bond scissions. We characterized the photoproducts and utilized the photoreaction to design a caged γ-aminobutyric acid (GABA) derivative that can release GABA upon irradiation in the visible range (>450 nm). This allowed us to stimulate neural cells in mouse brain slices.

本文言語	English
ページ（範囲）	1233-1240
ページ数	8
ジャーナル	ChemBioChem
DOI	https://doi.org/10.1002/cbic.201600097
出版ステータス	Published - 2016 7月 1
外部発表	はい

ASJC Scopus subject areas

生化学
分子医療
分子生物学
有機化学

文献へのアクセス

10.1002/cbic.201600097

他のファイルとリンク

引用スタイル

@article{ff56b10213ec455a92b99dd95cb9f925,

title = "Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA",

abstract = "Investigation of the unexpected photo-instability of 2,6-sulfonamide-substituted derivatives of the boron dipyrromethene (BODIPY) fluorophore led to the discovery of a photoreaction accompanied by multiple bond scissions. We characterized the photoproducts and utilized the photoreaction to design a caged γ-aminobutyric acid (GABA) derivative that can release GABA upon irradiation in the visible range (>450 nm). This allowed us to stimulate neural cells in mouse brain slices.",

keywords = "BODIPY, cage compounds, chemical biology, photolysis, sulfonamides",

author = "Aoi Takeda and Toru Komatsu and Hiroshi Nomura and Masamitsu Naka and Norio Matsuki and Yuji Ikegaya and Takuya Terai and Tasuku Ueno and Kenjiro Hanaoka and Tetsuo Nagano and Yasuteru Urano",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = jul,

day = "1",

doi = "10.1002/cbic.201600097",

language = "English",

pages = "1233--1240",

journal = "ChemBioChem",

issn = "1439-4227",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

AU - Takeda, Aoi

AU - Komatsu, Toru

AU - Nomura, Hiroshi

AU - Naka, Masamitsu

AU - Matsuki, Norio

AU - Ikegaya, Yuji

AU - Terai, Takuya

AU - Ueno, Tasuku

AU - Hanaoka, Kenjiro

AU - Nagano, Tetsuo

AU - Urano, Yasuteru

PY - 2016/7/1

Y1 - 2016/7/1

N2 - Investigation of the unexpected photo-instability of 2,6-sulfonamide-substituted derivatives of the boron dipyrromethene (BODIPY) fluorophore led to the discovery of a photoreaction accompanied by multiple bond scissions. We characterized the photoproducts and utilized the photoreaction to design a caged γ-aminobutyric acid (GABA) derivative that can release GABA upon irradiation in the visible range (>450 nm). This allowed us to stimulate neural cells in mouse brain slices.

AB - Investigation of the unexpected photo-instability of 2,6-sulfonamide-substituted derivatives of the boron dipyrromethene (BODIPY) fluorophore led to the discovery of a photoreaction accompanied by multiple bond scissions. We characterized the photoproducts and utilized the photoreaction to design a caged γ-aminobutyric acid (GABA) derivative that can release GABA upon irradiation in the visible range (>450 nm). This allowed us to stimulate neural cells in mouse brain slices.

KW - BODIPY

KW - cage compounds

KW - chemical biology

KW - photolysis

KW - sulfonamides

UR - http://www.scopus.com/inward/record.url?scp=84977080455&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84977080455&partnerID=8YFLogxK

U2 - 10.1002/cbic.201600097

DO - 10.1002/cbic.201600097

M3 - Article

C2 - 27038199

AN - SCOPUS:84977080455

SN - 1439-4227

SP - 1233

EP - 1240

JO - ChemBioChem

JF - ChemBioChem

ER -

Unexpected Photo-instability of 2,6-Sulfonamide-Substituted BODIPYs and Its Application to Caged GABA

抄録

ASJC Scopus subject areas

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル